Unemployed and depressed, Robert Samuel turned to Craigslist. It was iPhone release day in 2012 and, looking to make a few bucks, he offered to hold an Apple loyalist’s place in line for $100. Apple fever was strong, and Samuel quickly found a taker and rushed to the Fifth Avenue shop in New York. The man who hired him ended up being able to score the smart phone online but paid him anyway.

“I was going to leave (the line),” Samuel recalled. “It was actually a customer who prompted me to stay,” proposing, “Why don’t you sell your spot?”

Samuel realized he had stumbled on a money-making scheme and called his friends to join him in line. By the end of the day, the crew had sold four spots and five milk crates, which exhausted Apple fans bought to sit on. The day of waiting earned Samuel enough money to buy his own iPhone 5.

“I always call myself an accidental entrepreneur,” said Samuel, 41. Today, he’s CEO of Same Ole Line Dudes LLC, his professional line-sitting service with dozens of employees, all independent contractors.

A Brooklyn native, Samuel spent his career working a slew of customer service, retail and security jobs, which he credits with preparing him for the customer-facing business he now runs.

Same Ole Line Dudes, or Line Dudes for short, charges $25 for the first hour of waiting and $10 for every additional half hour. There’s a minimum of two hours and a $5 hourly surcharge for inclement weather, either below freezing or about 100 degrees. The line sitters get 60 per cent of the fee, plus tips. Line Dudes fields 60 to 100 requests a month and experiences an uptick in the summer from tourists.

At first, Samuel wasn’t sure the business was sustainable. “I wasn’t even taking myself seriously,” he said. “I was throwing paint on the wall and calling it something when it dried.”

Then the Cronut was invented.

Samuel’s business surged when a pastry chef combined the croissant with the doughnut and started selling an extremely limited supply at his SoHo bakery. Every day, Samuel would post on Craiglist offering to stand in line for it. With more clients than he could handle, he recruited his friends to stand in line with him, since the bakery limited the number of Cronuts per customer. He charged $60 to purchase and deliver two Cronuts, which retailed for $5 apiece.

Reporters noticed that Samuel and his buddies were at the bakery daily, and his line-sitting services made the local news. He once delivered Cronuts to a customer in Baltimore, who paid for his round trip on Amtrak.

His meticulous attention to detail spurred the company’s success but he acknowledges it has curbed expansion

“People started calling us for other stuff,” Samuel said. He began waiting in line for Saturday Night Live tapings, for famous speakers, for anything that created a queue. By early 2014, Samuel had launched a website for booking line-sitting appointments but still felt unsure about leaving his day job. He finally made running Line Dudes his full-time gig in January.

Hamilton was Samuel’s next Cronut. The Broadway musical was selling out, and scalpers were making thousands of dollars a ticket. People desperate to get in would line up at the midtown theatre, even in the dead of winter.

That’s when Samuel ordered the Line Dudes-branded tents that became his company’s calling card. Line sitters bring these along when they have to spend at least eight hours outside or wait overnight, and in bad weather. The bright yellow little tents are a fixture at sample sales and Instagram-famous restaurants, as well as Broadway ticket lines.

“I didn’t want to put myself at risk, and my team at risk,” Samuel said, “so we needed to have something that protected us from the elements.” In strong winter winds, it can feel as much as 40 degrees warmer inside the tents than outside, and they’re not a bad marketing vehicle either.

Samuel expects the sitters to carry a spare phone battery, a chair for sits of up to four hours, and a sleeping bag for more than four. Phones are typically loaded with Netflix, Hulu and a deep music collection. One line sitter, a law student, spent a long Hamilton wait studying for the bar, his tent filled with textbooks.

Today, Line Dudes includes neighbours, college students, retirees, veterans, soon-to-be lawyers, single parents — anyone punctual and willing to stand in line. The company has about 35 independent contractors on staff at any given time and is always adding more.

Sitters are generally personable. They pass the time making friends with the people around them, whom Samuels calls “the line family.” Occasionally, mostly at concert and theatre venues, the Line Dudes are mistaken for scalpers, and building a line family around you helps to set the record straight. “We squash that,” he said.

Things go awry, like when a client orders one sitter and then shows up with two friends to take over the spot. “We will not relinquish the spot to you if you come with people, and you won’t receive a refund,” Samuel said. He has no tolerance for line cutting. Every once in a while, a line sitter won’t show up or will come too late to get a good spot. In cases like that, Samuel usually waives the fee and offers the customer a free sit in the future.

Despite his large staff of contractors, Samuel is very much a one-man operation. He maintains the website, assigns line sitters to jobs, handles the finances and fields press requests, which are frequent and often international. A handful of more senior line sitters help handle the flow of emails and phone calls from customers. Samuel has declined to take on investors, though he said he’s had many offers.

“The beauty of this is that it’s low-overhead,” he said. “I work out of my living room. We pay for branded hats, we pay for the tents, the business cards.”

The beauty of this is that it’s low-overhead

A self-described micro-manager, Samuel credits his meticulous attention to detail with the company’s success but acknowledges it has curbed expansion. He regularly gets requests for his services in other cities, mainly San Francisco, Los Angeles and Atlanta, but currently operates only in New York. “I know that growth should be on my radar,” he said.

In the meantime, he’s working to perfect his services in the city and add clients. He encourages his staff to try everything they stand in line for, to bring a certain expertise to their services. Samuel has seen Hamilton seven times and tried every flavour of Cronut. He can recommend the best cookie dough at DŌ and offers a spirited review of Tony-winning Dear Evan Hansen. “When people call, I know what I’m talking about,” he said.

There’s no line Samuel won’t stand in, but there is a request that boggles his mind, even five years in: paying someone to stand in line for a free product. Line Dudes were recently hired to hold picnic tables at Brooklyn Bridge Park. In another instance, they were paid $65 for a three-hour wait to obtain a free Star Wars poster. “If they want to pay for it, we will go,” he said.

In a sea of requests for tickets, doughnuts and milkshakes, the Dudes occasionally get more serious work. The company has been hired for the past two years by parents to wait in line at a New Jersey pre-kindergarten program that aims to teach children compassion and respect. Fewer than 100 spots are available, and they waited for over two days on behalf of clients, a sit of almost $1,000 a person.

“It’s something meaningful. It’s not a food item, it’s not the latest gadget,” Samuel said. “I hold that very dear.”